Islamorada Holidays
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Where to stay in Islamorada
Find the best Islamorada areas and neighborhoods for the activities you enjoy most. Learn more about Islamorada
Matecumbe
6 out of top 10 points of interest in this area
If you're spending some time in Matecumbe, Bud n' Mary's Dive Center and Robbie’s of Islamorada are top sights worth seeing.
Top hotels in Islamorada
Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82 Islamorada FL
Fully refundableReserve now, pay when you stay
The price is 7.140.967 ₫ per night from 18 Jun to 19 Jun
7.140.967 ₫
9.959.174 ₫ total
18 Jun - 19 Jun
includes taxes & fees
9.2/10 Wonderful! (1,314 reviews)
"great place to be"
Reviewed on 1 Jun 2026
Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
The price is 5.228.020 ₫ per night from 8 Jun to 9 Jun
5.228.020 ₫
7.362.641 ₫ total
8 Jun - 9 Jun
includes taxes & fees
9.2/10 Wonderful! (1,736 reviews)
"This place is perfect"
Reviewed on 1 Jun 2026
Islander Resort
82100 Overseas Highway Islamorada FL
Fully refundableReserve now, pay when you stay
The price is 5.611.663 ₫ per night from 30 Jun to 1 Jul
5.611.663 ₫
8.090.465 ₫ total
30 Jun - 1 Jul
includes taxes & fees
9.4/10 Exceptional! (1,030 reviews)
"Would definitely stay there, again!"
Reviewed on 3 Jun 2026
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Popular places to visit
Founders Park
3.5/5(2 reviews)
Enjoy the beautiful sunsets and explore Founders Park, a lovely green space in Islamorada. Wander through the seaside and beautiful beaches in this family-friendly area.
Anne's Beach
4.5/5(3 reviews)
If a restful holiday is part of your travel plans, Anne's Beach might be the perfect place to visit during your trip to Islamorada.
Bud n' Mary's Dive Center
4.5/5(3 reviews)
Explore the waterfront of Bud n' Mary's Dive Center and enjoy other activities such as fishing in Islamorada. Discover the beautiful sunsets and seafood restaurants in this family-friendly area.
